Palladium‐Catalzyed Atroposelective 16‐Membered Macrocyclization: Total Synthesis of Isoplagiochin D
Palladium‐Catalzyed Atroposelective 16‐Membered Macrocyclization: Total Synthesis of Isoplagiochin D
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钯催化的 Atroposelective 16-Membered 大环化：Isoplagiochin D 的全合成
DOI：
10.1002/cjoc.202000051
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Zhenhua Gu
中科院分区：
文献类型：
--
作者：
Junwei Xi;Zhenhua Gu
主要观察结果和结论摘要异枝藻素D是一种环应变大环双联苄基，其在一个联芳基结构中显示稳定的轴向手性，而在另一个联芳基结构中显示半稳定的轴向手性。我们在这里报道了一个前所未有的例子，通过Pd催化的苄基卤和卡宾之间的大环化催化不对称合成环应变阻转异构体。这种新开发的Pd催化的不对称大环化方案使我们能够以高度对映选择性的方式快速合成异枝菌素D。
Summary of main observation and conclusionIsoplagiochin D is a ring‐strained macrocyclic bisbibenzylis, which showed stable axial chirality in one biaryl structure, and semistable axial chirality in the other biaryl moiety. We reported here an unprecedented example for the catalytically asymmetric synthesis of ring‐strained atropisomers via Pd‐catalyzed macrocyclization between benzyl halides and carbenes. This newly developed Pd‐catalyzed asymmetric macrocyclization protocol enabled us a quick synthesis of isoplagiochin D in a highly enantioselective manner.